Every team, venture, and startup has a story to tell. In this special edition of Venture unscripted., podcast host Josh Barker looks inward at City Innovations’ team to pick the brain of Thad Senti, Chief Digital Officer at the company.
Thad has a unique entrepreneurial history and brings a special kind of experience and perspective to the table that makes City Innovations a strong team. He also goes in-depth about how his career started, how his company first launched, and tips for entrepreneurs when first creating their venture.
Listen to the podcast video below or keep scrolling to read the podcast recap.
Nearly 30 Years in Tech
Thad has been in the development and technology sector for nearly 30 years, but originally thought he would become a high school biology teacher. However, that didn’t end up being the path he followed.
“I was already around computers growing up and enjoyed them,” Thad explained. “But I didn’t really see them as something you could have a career around.”
At the time, computers were something to “play with” and not necessarily used to program. But when Thad was introduced to Commodore VIC-20 and some basic programming language by a middle school friend, his mind was blown.
Thad eventually taught himself some basic programming — he was always very entrepreneurial, even as a young kid.
“I’ve always had this mindset,” he explained. “I wanted to own the business, I wanted to be in control of my own destiny.”
And that is what drove him into computer software. He decided to become a consultant and write software.
Eventually, Thad worked his way up to getting paid to develop software in the research field — so there was no limit to what he would develop and what he could.
“We ended up building something on top of Windows 3.0,” Thad explained. “And I got a lot of experience in things like user experience design, customer experience design, and all that kind of stuff.”
Everything that Thad had taught himself and learned on the job landed him a full-time job at Utah State University where he taught graduate students computer programming, as an undergraduate student himself. The professor that Thad worked for also happened to be an entrepreneur who owned his own business. The two decided to form a company together.
The Next Phase
Thad and his partner initially thought their company would build software around hydraulics. They even had a contract with the Department of Transportation. That work didn’t go very far, but there were plenty of interesting projects to follow.
Eventually, Thad’s company phased into learning management systems and writing certification simulations — until they were connected to the Education Department. Thad’s work was integral to revolutionizing certifications. He worked on ways to provide candidates with the actual software, modifying user interfaces, and updating permissions that landed his company several contracts through companies like Microsoft, Novell, WordPerfect, IBM, Intell, and Oracle.
Thad’s journey lead him down a path that forced him to really think about how he would build software, and on an enterprise level.
“It wasn’t just like, ‘I’m going to build this hydraulics calculator,’” Thad explained. “You’re looking at software, the most sophisticated software that was out there at the time, and figuring out how we’re going to make all this software come together.”
Thad said he ran into some challenges with scale — the more he poured into the simulator, the bigger the software got.
The Go-To-Market Strategy
At every turn, Thad utilized strong connections. Then his work snowballed.
“It was all quite by accident,” Thad explained. “We didn’t think very hard about how we would market. We just thought we were tool builders and we knew exactly what [the customers] wanted. But we ran into all kinds of weird user problems.”
But every step of the journey was a good experience, whether there was success or failure.
Eventually, Thad bought out his business partner and moved the company to Denver. He brought in a team of developers and leaned into the simulation work. But Thad’s entrepreneurial spirit couldn’t be quelled.
“I started talking with a director at Microsoft about forming a business together,” Thad explained. His future business partner had several contracts and work inside of Microsoft and pitched expanding Thad’s business to see how far they could take it.
Big Deals, Bigger Stakes
Thad began developing simulations and getting bigger and bigger deals. He worked on Microsoft’s exam distribution software and learned that the competitor’s software was performing better and requiring fewer resources.
“We caught wind of that and through my connection, we started talking on the sly about building something better,” Thad explained.
And they did. They got the software in front of the CEO of Sylvan Prometrics (known today as Prometrics). Thad and his business partner put together a big presentation on getting the CEO to make their software the foundation for his testing centers.
“In my mind, I’m thinking at this time, ‘I’m married and have a five-year-old and a one-year-old’ — a very young family,” Thad said. “I’m still very much in the throes of building software but my business partner has the business sense to know what to go for.”
Thad and his partner didn’t think in “terms of today” — they were flying by the seat of their pants. What Thad thought would be a $500,000 deal turned into a $17.3 million deal.
“I look over to the CEO and he’s not even batting an eye,” Thad explained. At this point, the finish line was in sight. But that was not actually the case.
The CEO calls the duo and explains that the deal isn’t going to go through. They receive a call from Microsoft, who had gotten word of their deal and potentially causing them to back out of their current deal with Sylvan Prometrics. Sylvan Prometrics decidedly didn’t want to lose Microsoft’s contract over two seemingly unknown developers.
“So we went from zero to riches back to rags in the course of about four weeks,” Thad explained. “And it took me a long time to understand why someone wouldn’t pick the better technology.”
But business is much more complicated and the stakes are often much higher than “the better technology is the one that should win.”
Thad looks back at the series of events and knows how he would have done things differently. “We would have approached Microsoft first and pitched them, ‘How do we help you look good? How do we improve your software?’ Without upsetting the obvious politics of doing business. We just didn’t see that coming.”
What Happened Next?
As Thad winds down this story, a couple of things happened that eventually put an end to his company. Many reverted away from the more sophisticated software. The simpler programs ran much easier and didn’t require a lot of resources or technology to make things happen.
“We just kind of saw our business dry up,” Thad explained. “And Microsoft was pretty angry with us, so we saw that dry out as well.”
“We were too loud about how great we were,” he continued. “And we were good, but we were beating our drum pretty loudly and we weren’t paying attention to the people that were going to be threatened or hurt by what we were doing.”
A Learning Experience
Thad has learned so much from the experience and imparts his wisdom to other entrepreneurs out there.
“Build the right thing,” Thad started. “I think that’s a very good principle going forward because you save yourself a lot of money. We went down a lot of dead ends trying to build what we thought was the right thing without speaking to anybody about it.”
Thad also suggested understanding the players in the environment you’re entering into. Knowing the right people and having the right advocates can make all the difference in success or failure, even if you don’t have the most perfect solution.
Finally, Thad closed out the interview by reminding everyone to never stop trying.
“You’re going to fail, and it sounds cliche, but try again,” he said. “Take a break from it if you’re burnt out, but if you are truly an entrepreneur and you’ve got it in your heart, it never just goes away. It’s just kind of in your blood if you have that creative desire to build something and own it.”
Continue Learning
Listen to the full story and gain even more advice for entrepreneurs by listening to the full podcast video below.
For more Venture unscripted. podcasts, click here.
